US8008854B2 - Light emitting material and light emitting diode device - Google Patents
Light emitting material and light emitting diode device Download PDFInfo
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- US8008854B2 US8008854B2 US12/340,773 US34077308A US8008854B2 US 8008854 B2 US8008854 B2 US 8008854B2 US 34077308 A US34077308 A US 34077308A US 8008854 B2 US8008854 B2 US 8008854B2
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- emitting material
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- 239000000463 material Substances 0.000 title claims abstract description 83
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 42
- 229920002098 polyfluorene Polymers 0.000 claims abstract description 24
- 239000000126 substance Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 46
- 0 [1*]C1([2*])C2=CC(C)=CC=C2C2=CC=C([Ar]C)C=C21 Chemical compound [1*]C1([2*])C2=CC(C)=CC=C2C2=CC=C([Ar]C)C=C21 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- JJUBUOUYIDDVKL-UHFFFAOYSA-N C1=CC2=NSN=C2C=C1.C1=CSC(C2=CC=C(C3=CC=CS3)C3=NSN=C23)=C1 Chemical compound C1=CC2=NSN=C2C=C1.C1=CSC(C2=CC=C(C3=CC=CS3)C3=NSN=C23)=C1 JJUBUOUYIDDVKL-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- ILRABTMSQOHSCR-UHFFFAOYSA-N C#CC#CC#COC1=CC(C)=C(C=O)C=C1C.CCCCC1=CC=C(C2=CC=C(C3=CC(O)=C(C4=CC=C(C5=CC=CC=C5)C=C4)C=C3OC)C=C2)C=C1.[HH].[HH].[HH].[HH].[HH].[HH].[HH] Chemical compound C#CC#CC#COC1=CC(C)=C(C=O)C=C1C.CCCCC1=CC=C(C2=CC=C(C3=CC(O)=C(C4=CC=C(C5=CC=CC=C5)C=C4)C=C3OC)C=C2)C=C1.[HH].[HH].[HH].[HH].[HH].[HH].[HH] ILRABTMSQOHSCR-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- PHXYCFKGGCSYAF-UHFFFAOYSA-N C#CC#CC#COC1=CC(C)=C(C=O)C=C1C.COC1=CC(C2=CC=C(C3=CC=CC=C3)C=C2)=C(O)C=C1C1=CC=C(C2=CC=C(C)C=C2)C=C1.[HH].[HH].[HH].[HH].[HH].[HH].[HH] Chemical compound C#CC#CC#COC1=CC(C)=C(C=O)C=C1C.COC1=CC(C2=CC=C(C3=CC=CC=C3)C=C2)=C(O)C=C1C1=CC=C(C2=CC=C(C)C=C2)C=C1.[HH].[HH].[HH].[HH].[HH].[HH].[HH] PHXYCFKGGCSYAF-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- WJRFOSBCACMRMM-UHFFFAOYSA-N 9H-fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 WJRFOSBCACMRMM-UHFFFAOYSA-N 0.000 description 1
- JJEPYXPNPATWHY-UHFFFAOYSA-N C#CC#CC#COC1=CC(Br)=C(C=O)C=C1Br.CCCCC1=CC=C(C2=CC=C(C3=CC(O)=C(C4=CC=C(C5=CC=CC=C5)C=C4)C=C3OC)C=C2)C=C1.[HH].[HH].[HH].[HH].[HH].[HH].[HH] Chemical compound C#CC#CC#COC1=CC(Br)=C(C=O)C=C1Br.CCCCC1=CC=C(C2=CC=C(C3=CC(O)=C(C4=CC=C(C5=CC=CC=C5)C=C4)C=C3OC)C=C2)C=C1.[HH].[HH].[HH].[HH].[HH].[HH].[HH] JJEPYXPNPATWHY-UHFFFAOYSA-N 0.000 description 1
- -1 borate ester Chemical class 0.000 description 1
- XGERJWSXTKVPSV-UHFFFAOYSA-N c1c[s]c(-c2ccc(-c3ccc[s]3)c3n[s]nc23)c1 Chemical compound c1c[s]c(-c2ccc(-c3ccc[s]3)c3n[s]nc23)c1 XGERJWSXTKVPSV-UHFFFAOYSA-N 0.000 description 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N c1cc2n[s]nc2cc1 Chemical compound c1cc2n[s]nc2cc1 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 238000002875 fluorescence polarization Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- QZGIWPZCWHMVQL-UIYAJPBUSA-N neocarzinostatin chromophore Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3([C@@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-UIYAJPBUSA-N 0.000 description 1
- 238000000904 thermoluminescence Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/868—Arrangements for polarized light emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
Definitions
- the present invention generally relates to a light emitting material and a light emitting diode device, in particular, to a light emitting material capable of emitting polarized light and a light emitting diode (LED) device manufactured using the same.
- a light emitting material capable of emitting polarized light
- LED light emitting diode
- a light emitting diode is a semiconductor device that is mainly made of a semiconductor material of III-V group of elements compound. Such a semiconductor material is capable of convert electric energy into light. In specific, when a current is applied to such a semiconductor material, electrons within the semiconductor material combine with holes, and excess energy is released as light, thereby achieving the light emitting effect.
- the lifespan of the LED may be up to about 100,000 hours, and no idling time is required.
- the LED can be applied in a wide variety of fields, such as scanner light sources requiring for a fast response, back lights of liquid crystal displays (LCDs), illumination for instrument panels of vehicles, traffic signal lamps, and ordinary illuminators.
- LCDs liquid crystal displays
- the LCDs need to use polarized light as the display light source.
- advantages of the LED such as small volume, low power consumption and capable of mass production enable the LCDs to be considerably convenient and competitive, all light sources available on the market, including the LED, are suitable for emitting non-polarized light. Therefore, when designing an LCD, a polarizing plate has to be disposed between the back light and an LCD panel. In such a manner, the volume and fabricating cost of the LCDs cannot be further reduced.
- the present invention is directed to a light emitting material, so as to solve the problem that the light emitted by ordinary light emitting materials is not polarized.
- the present invention is also directed to a light emitting diode (LED) device, so as to emit polarized light.
- LED light emitting diode
- the present invention provides a light emitting material, which includes a polyfluorene derivative having an aromatic ring containing a liquid crystal side group.
- the polyfluorene derivative has a chemical structure of formula 1:
- Ar is the aromatic ring containing the liquid crystal side group
- R 1 and R 2 are alkyls
- n is 20 to 500.
- the liquid crystal side group is, for example, a chain of five benzene rings.
- the chain of five benzene rings has a chemical structure of formula 2:
- the light emitting material further includes a plurality of chromophores bonded to the polyfluorene derivative.
- the chromophores have a chemical structure of at least one of formula 3 and formula 4:
- the present invention also provides an LED device, which includes a substrate, a first electrode, a conductive alignment layer, a light emitting material layer, and a second electrode.
- the first electrode is disposed on the substrate, and the conductive alignment layer is disposed on the first electrode.
- the light emitting material layer is disposed on the conductive alignment layer.
- the light emitting material layer includes a polyfluorene derivative having an aromatic ring containing a liquid crystal side group.
- the polyfluorene derivative has a chemical structure of formula 1:
- Ar is the aromatic ring containing the liquid crystal side group
- R 1 and R 2 are alkyls
- n is 20 to 500.
- the second electrode is disposed on the light emitting material layer.
- one of the first electrode and the second electrode is, for example, a transparent electrode. Meanwhile, the other of the first electrode and the second electrode is, for example, a metal electrode.
- the conductive alignment layer is made of poly (3,4-ethylenedioxythiophene) (PEDOT).
- PEDOT poly (3,4-ethylenedioxythiophene)
- the liquid crystal side group is a chain of five benzene rings.
- the chain of five benzene rings has a chemical structure of formula 2:
- the LED device further includes a plurality of chromophores bonded to the polyfluorene derivative.
- the chromophores have a chemical structure of at least one of formula 3 and formula 4:
- the light emitting material includes, for example, a polyfluorene derivative having an aromatic ring containing a liquid crystal side group.
- the polyfluorene derivative has a chemical structure of formula 1:
- the polyfluorene derivative is, for example, formed by polymerization reaction of a first fluorene, a second fluorene, and a liquid crystal group.
- first fluorene and the second fluorene respectively have chemical structures of formula 1-a and formula 1-b:
- the first fluorene is, for example, a fluorene with a bromine atom
- the second fluorene is a fluorene with a boron atom
- the liquid crystal group may be a chain of five benzene rings.
- the chain of five benzene rings has, for example, a chemical structure of formula 1-c:
- the two fluorenes are bonded to each other through reacton between the borate ester of the second fluorene and the bromine of the first fluorene.
- the liquid crystal group is bonded to the second fluorene through reaction between the boron of the second fluorene and the bromine of the liquid crystal group.
- Ar of formula 1 is, for example, the liquid crystal group bonded to the polyfluorene derivative through polymerization.
- the liquid crystal side group has been bonded into the polyfluorene derivative through reaction between the bromine atom of the original liquid crystal group and the boron atom of the second fluorene. Therefore, Ar has, for example, a chemical structure of formula 2:
- both the first fluorene and the liquid crystal group need to react with and be bonded to the second fluorene.
- the weight percentage (wt %) of the second fluorene is, for example, 50%
- the total wt % of the first fluorene and the liquid crystal group is, for example, 50%.
- the wt % of the first fluorene and that of the liquid crystal group may be respectively 40% and 10%, 30% and 20%, or 10% and 40%. It should be understood that these content ratios are merely given by way of example, and are not intended to limit the present invention.
- the light emitting material of this embodiemnt is synthesized by, for example, the Suzuki coupling method.
- the light emitted by fluorene is blue. Therefore, in other embodiments, when fabricating the light emitting material, different chromophores can be added such that the chromophores are bonded to the polyfluorene derivative, in order to enable the light emitting material of this embodiemnt to emit light of other colors.
- the chromophores may have a chemical structure of at least one of formula 3 and formula 4:
- the light emitting material A can, for example, emit green light, while the light emitting material B can, for example, emit red light.
- the present invention is not limited to the chromophores of formula 3 and formula 4, and any material that can provide color adjustment and can be polymerized with the second fluorene is capable to be used as the chromophore of the present invention.
- the average molecular weight of the light emitting materials provided in the present invention is about 10,000 to 100,000, and the high molecular diffusivity is about 1.10 to 2.00. Since the light emitting materials of this kind can possess a good film-forming property, the light emitting materials of the present invention can be formed in a device by a spin-coating method. That is, the light emitting materials of the present invention is apt to simplify the device fabricating process, as compared to an ordinary light emitting material having a low molecular weight that must be formed in a device by vacuum evaporation. Moreover, it is found from the experimental results that the fluorescence polarization ratios of the light emitting materials of the present invention are all greater than 10. In other words, the light emitting materials of the present invention have a fairly good polarization property and can thus provide polarized light.
- FIG. 1 shows an LED device according to an embodiment of the present invention.
- an LED device 100 includes a substrate 110 , a first electrode 120 , a conductive alignment layer 130 , a light emitting material layer 140 , and a second electrode 150 .
- the first electrode 120 is disposed on the substrate 110
- the conductive alignment layer 130 is disposed on the first electrode 120 .
- the light emitting material layer 140 is disposed on the conductive alignment layer 130
- the second electrode 150 is disposed on the light emitting material layer 140 .
- the light emitting material layer 140 is made of any one or more selected from the group consisting of the light emitting materials of the above embodiments.
- the light emitting material that the light emitting material layer is made of is substantially a polyfluorene derivative having a liquid crystal side group.
- the LED device 100 can emit light of various different colors.
- the conductive alignment layer 130 may, for example, have an alignment structure suitable for orientation of the light emitting material.
- the LED device 100 can provide polarized light having a particular polarization character. If such an LED device 100 is applied to an apparatus such as an LCD that requires for particular polarized light to serve as a light source, it helps to simplify the device design. For example, if an LCD uses the LED device 100 of this embodiemnt as a light source, the LCD can utilize the light source having a polarity to display without additonally disposing a lower polarizing plate.
- the conductive alignment layer 140 is made of, for example, PEDOT.
- One of the first electrode 130 and the second electrode 150 is, for example, a transparent electrode, and the other of the first electrode 130 and the second electrode 150 is, for example, a metal electrode.
- the LED device 100 emits light, the light is, for example, diverged outward from one side of the transparent electrode. In other words, this embodiment is not intended to limit whether the LED device 100 emits the light from the first electrode 130 to the substrate 110 or emits the light from the second electrode 150 to a direction away from the substrate 110 .
- the LED device 100 is, for example, fabricated by the following steps.
- the first electrode 120 is formed on the substrate 110 .
- the first electrode may be made of a transparent conductive material or a metal, and in this embodiment, the transparent conductive material is taken as an example.
- the conductive alignment layer 130 is formed on the first electrode 120 . Meanwhile, a rubbing process is performed so as to form a suitable alignment structure in the conductive alignment layer 130 .
- one or a combination of the above light emitting materials is formed on the conductive alignment layer 130 by a spin-coating method. Accordingly, the light emitting material is solidified into the light emitting material layer 140 .
- the LED device 100 since the light emitting material is solidified into the light emitting material layer 140 in a particular orientation manner, the light emitted by the LED device 100 is influenced by optical properties of the liquid crystal side group and thus presents a particular polarization character. That is, the LED device 100 of this embodiment can provide polarized light without cooperating with additional polarizing apparatuses. Therefore, the LED device 100 can solve the problem in the prior art that the volume of the device cannot be reduced since the light source needs to cooperate with a polarizing apparatus in order to provide polarized light.
- the present invention enables the light emitting material to have a liquid crystal side group, the light emitting material has the properties of liquid crystal molecules such as orientation and polarity.
- the LED device can emit polarized light.
- the LED device of the present invention can provide polarized light without cooperating with additional polarizing apparatuses, thereby being apt to improve the practicability of the LED device.
- the light emitting material of the present invention helps to simplify the manufacturing of the device due to its good film-forming property.
Abstract
-
- wherein Ar is an aromatic ring containing the liquid crystal side group, R1 and R2 are alkanes and n is 20 to 500.
Description
Ar is the aromatic ring containing the liquid crystal side group, R1 and R2 are alkyls, and n is 20 to 500.
Ar is the aromatic ring containing the liquid crystal side group, R1 and R2 are alkyls, and n is 20 to 500. The second electrode is disposed on the light emitting material layer.
Ar is the aromatic ring containing the liquid crystal side group, R1 and R2 are alkyls, and n is 20 to 500. In practice, in an embodiment, R1 and R2 may be C8H17.
Chromo- | |||||
phore | Chromophore | Liquid | |||
First | Second | of | of | Crystal | |
Material | Fluorene | Fluorene | Formula 3 | Formula 4 | Group |
Light | 15% | 50% | 15% | 0% | 20% |
Emitting | |||||
Material A | |||||
Light | 15% | 50% | 10% | 5% | 20% |
Emitting | |||||
Material B | |||||
Claims (9)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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TW97134456 | 2008-09-08 | ||
TW97134456A | 2008-09-08 | ||
TW097134456A TW201011089A (en) | 2008-09-08 | 2008-09-08 | Light emitting material and light emitting diode device |
Publications (2)
Publication Number | Publication Date |
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US20100060146A1 US20100060146A1 (en) | 2010-03-11 |
US8008854B2 true US8008854B2 (en) | 2011-08-30 |
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US12/340,773 Expired - Fee Related US8008854B2 (en) | 2008-09-08 | 2008-12-22 | Light emitting material and light emitting diode device |
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TW (1) | TW201011089A (en) |
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2008
- 2008-09-08 TW TW097134456A patent/TW201011089A/en unknown
- 2008-12-22 US US12/340,773 patent/US8008854B2/en not_active Expired - Fee Related
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US7220040B2 (en) | 2004-11-12 | 2007-05-22 | Harris Corporation | LED light engine for backlighting a liquid crystal display |
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TW201011089A (en) | 2010-03-16 |
US20100060146A1 (en) | 2010-03-11 |
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